158 total properties
Did you mean the neighborhood Oakland?
View 127 Jeffrey Lane # 18C Oakland, MD MLS# MDGA2011056
    Save 127 Jeffrey Lane # 18C Oakland, MD MLS# MDGA2011056
    1 of 40
    $275,000
    3

    Beds

    2.0

    Baths

    875

    Sq.Ft.

    127 Jeffrey Lane # 18C

    Oakland, MD

    Bright
    Courtesy of RAILEY REALTY, INC.
    View 26 Green Brier Road Oakland, MD MLS# MDGA2011050
      Save 26 Green Brier Road Oakland, MD MLS# MDGA2011050
      1 of 19
      $295,000
      Studio

      Beds

      0.0

      Baths

      26 Green Brier Road

      Oakland, MD

      Bright
      Courtesy of RAILEY REALTY, INC.
      View 26 Green Brier Road Oakland, MD MLS# MDGA2011054
        Save 26 Green Brier Road Oakland, MD MLS# MDGA2011054
        1 of 19
        $295,000

        26 Green Brier Road

        Oakland, MD

        Bright
        Courtesy of RAILEY REALTY, INC.
        The time to sell is now! THE TIME TO SELL IS NOW!
        View Hammond Street Oakland, MD MLS# MDGA2011044
          Save Hammond Street Oakland, MD MLS# MDGA2011044
          1 of 2
          $29,900
          Studio

          Beds

          0.0

          Baths

          Hammond Street

          Oakland, MD

          Bright
          Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
          View 729 E Oak Street Oakland, MD MLS# MDGA2011048
            Save 729 E Oak Street Oakland, MD MLS# MDGA2011048
            1 of 62
            $185,000
            3

            Beds

            1.1

            Baths

            1,170

            Sq.Ft.

            729 E Oak Street

            Oakland, MD

            Bright
            Courtesy of RAILEY REALTY, INC.
            View 267 San Francisco Street Oakland, MD MLS# MDGA2011040
              Save 267 San Francisco Street Oakland, MD MLS# MDGA2011040
              1 of 30
              $899,900
              4

              Beds

              2.1

              Baths

              3,278

              Sq.Ft.

              267 San Francisco Street

              Oakland, MD

              Bright
              Courtesy of HOMESMART
              View Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036
              • Virtual Tour
              Save Glendale Rd Lot 12 Alpine Village Subdivision Oakland, MD MLS# MDGA2011036
              1 of 10
              $995,000
              Studio

              Beds

              0.0

              Baths

              Glendale Rd Lot 12 Alpine Village Subdivision

              Oakland, MD

              Bright
              Courtesy of RAILEY REALTY, INC.
              View Lots 34 & 35 Fox Tail Road Oakland, MD MLS# MDGA2011026
                Save Lots 34 & 35 Fox Tail Road Oakland, MD MLS# MDGA2011026
                1 of 11
                $5,000
                Studio

                Beds

                0.0

                Baths

                Lots 34 & 35 Fox Tail Road

                Oakland, MD

                Bright
                Courtesy of RAILEY REALTY, INC.
                View 43 Sloan Tract Road Oakland, MD MLS# MDGA2011032
                  Save 43 Sloan Tract Road Oakland, MD MLS# MDGA2011032
                  1 of 47
                  $299,000
                  4

                  Beds

                  2.0

                  Baths

                  1,743

                  Sq.Ft.

                  43 Sloan Tract Road

                  Oakland, MD

                  Bright
                  Courtesy of RAILEY REALTY, INC.
                  View 711 Heritage Drive Oakland, MD MLS# MDGA2011022
                    Save 711 Heritage Drive Oakland, MD MLS# MDGA2011022
                    1 of 58
                    $249,000
                    3

                    Beds

                    2.0

                    Baths

                    1,400

                    Sq.Ft.

                    711 Heritage Drive

                    Oakland, MD

                    Bright
                    Courtesy of RAILEY REALTY, INC.
                    View 232 Jeffrey Lane # 33 Oakland, MD MLS# MDGA2011030
                    • Virtual Tour
                    Save 232 Jeffrey Lane # 33 Oakland, MD MLS# MDGA2011030
                    1 of 39
                    $425,000
                    2

                    Beds

                    2.1

                    Baths

                    2,960

                    Sq.Ft.

                    232 Jeffrey Lane # 33

                    Oakland, MD

                    Bright
                    Courtesy of SAMSON PROPERTIES
                    View 1108 Hutton Road Oakland, MD MLS# MDGA2010986
                      Save 1108 Hutton Road Oakland, MD MLS# MDGA2010986
                      1 of 37
                      $199,000
                      2

                      Beds

                      1.0

                      Baths

                      960

                      Sq.Ft.

                      1108 Hutton Road

                      Oakland, MD

                      Bright
                      Courtesy of RAILEY REALTY, INC.
                      View 1359 Cedar Lane Oakland, MD MLS# MDGA2010974
                      • Virtual Tour
                      Save 1359 Cedar Lane Oakland, MD MLS# MDGA2010974
                      1 of 37
                      $275,000
                      2

                      Beds

                      1.1

                      Baths

                      1,440

                      Sq.Ft.

                      1359 Cedar Lane

                      Oakland, MD

                      Bright
                      Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
                      View 3395 Fingerboard Road Oakland, MD MLS# MDGA2010996
                      • New Construction
                      Save 3395 Fingerboard Road Oakland, MD MLS# MDGA2010996
                      1 of 20
                      $199,000
                      4

                      Beds

                      2.0

                      Baths

                      3395 Fingerboard Road

                      Oakland, MD

                      Bright
                      Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
                      View 931 Black Oak Drive Oakland, MD MLS# MDGA2010958
                        Save 931 Black Oak Drive Oakland, MD MLS# MDGA2010958
                        1 of 53
                        $359,000
                        3

                        Beds

                        1.0

                        Baths

                        990

                        Sq.Ft.

                        931 Black Oak Drive

                        Oakland, MD

                        Bright
                        Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
                        View 178 Winding Trail Lane # 5B Oakland, MD MLS# MDGA2010960
                          Save 178 Winding Trail Lane # 5B Oakland, MD MLS# MDGA2010960
                          1 of 47
                          $589,000
                          5

                          Beds

                          4.1

                          Baths

                          3,300

                          Sq.Ft.

                          178 Winding Trail Lane # 5B

                          Oakland, MD

                          Bright
                          Courtesy of RAILEY REALTY, INC.
                          View Lot 17 Birchwood Drive Oakland, MD MLS# MDGA2010950
                            Save Lot 17 Birchwood Drive Oakland, MD MLS# MDGA2010950
                            1 of 10
                            $5,000
                            Studio

                            Beds

                            0.0

                            Baths

                            Lot 17 Birchwood Drive

                            Oakland, MD

                            Bright
                            Courtesy of RAILEY REALTY, INC.
                            View 1358 Crellin Underwood Road Oakland, MD MLS# MDGA2010946
                              Save 1358 Crellin Underwood Road Oakland, MD MLS# MDGA2010946
                              1 of 37
                              $85,000
                              2

                              Beds

                              1.0

                              Baths

                              864

                              Sq.Ft.

                              1358 Crellin Underwood Road

                              Oakland, MD

                              Bright
                              Courtesy of RAILEY REALTY, INC.
                              View 5423 Gorman Road Oakland, MD MLS# MDGA2010906
                                Save 5423 Gorman Road Oakland, MD MLS# MDGA2010906
                                1 of 21
                                $275,000
                                720

                                Sq.Ft.

                                5423 Gorman Road

                                Oakland, MD

                                Bright
                                Courtesy of TAYLOR MADE DEEP CREEK VACATIONS & SALES
                                View 209 Glendale Road Oakland, MD MLS# MDGA2010922
                                  Save 209 Glendale Road Oakland, MD MLS# MDGA2010922
                                  1 of 89
                                  $2,100,000
                                  6

                                  Beds

                                  4.1

                                  Baths

                                  3,882

                                  Sq.Ft.

                                  209 Glendale Road

                                  Oakland, MD

                                  Bright
                                  Courtesy of RAILEY REALTY, INC.

                                  About Oakland

                                  Listings in Oakland, MD

                                  157

                                  Estimated median home price

                                  $295,000
                                  Oakland MD Homes for Sale & Properties

                                  Weichert Realtors is one of the nation's leading providers of Oakland, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Oakland, MD.

                                  Homes for Sale by Price in Oakland, MD

                                  PriceCount
                                  $0 - 100K35
                                  $100K - 200K22
                                  $200K - 300K26
                                  $300K - 400K13
                                  $400K - 500K8
                                  $500K - 600K10
                                  $600K - 700K10
                                  $700K - 800K8
                                  $800K - 900K4
                                  $900K - 1M2
                                  $1M - Max19

                                  Homes for Sale by Type in Oakland, MD

                                  Property TypeCount
                                  Single Family64
                                  Townhouse2
                                  Condo22
                                  Commercial13
                                  Rental4
                                  Lots and Land56
                                  Condo/Town/CoOp0
                                  CoOp0
                                  Multi Family0
                                  Mobile Home0
                                  Farms0

                                  (Data as of 2/23/2026)

                                  Find Properties in Oakland, MD

                                  Oakland, MD Information

                                  Find Properties by Zip

                                  Information deemed reliable but not guaranteed.

                                  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

                                  Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

                                  The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

                                  Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.

                                  © 2026 BrightMLS. All Rights Reserved.